CN109942480A - A kind of synthetic method of aromatic ring diindyl -5- alcohol compound - Google Patents
A kind of synthetic method of aromatic ring diindyl -5- alcohol compound Download PDFInfo
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- CN109942480A CN109942480A CN201910370037.6A CN201910370037A CN109942480A CN 109942480 A CN109942480 A CN 109942480A CN 201910370037 A CN201910370037 A CN 201910370037A CN 109942480 A CN109942480 A CN 109942480A
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- diindyl
- alcohol compound
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- phenyl
- aromatic ring
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 15
- 238000010189 synthetic method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
- ZQDVHEWFWFAZKK-UHFFFAOYSA-N 1-oxidobenzo[g]indol-1-ium-5-one Chemical compound [N+]=1(C=CC2=CC(C3=C(C=12)C=CC=C3)=O)[O-] ZQDVHEWFWFAZKK-UHFFFAOYSA-N 0.000 claims abstract description 5
- NMSLUAZZTFUUFZ-UHFFFAOYSA-N 2h-thiophen-5-one Chemical compound O=C1SCC=C1 NMSLUAZZTFUUFZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 18
- 235000011054 acetic acid Nutrition 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- -1 substituted-phenyl Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 238000010523 cascade reaction Methods 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 229910000510 noble metal Inorganic materials 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000000605 extraction Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000000191 1,4-naphthoquinones Chemical class 0.000 description 1
- JVMUPDOMGALPOW-UHFFFAOYSA-N 4-methoxynaphthalen-1-amine Chemical compound C1=CC=C2C(OC)=CC=C(N)C2=C1 JVMUPDOMGALPOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Abstract
The invention discloses a kind of synthetic methods of aromatic ring diindyl -5- alcohol compound, belong to technical field of organic synthesis.Technical solution of the present invention main points are as follows:
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of synthesis of aromatic ring diindyl -5- alcohol compound
Method.
Background technique
Benzindole -5- alcohol compound not only has significant bioactivity, but also as intermediate many fine
It is widely used in the synthesis of chemicals.Based on its importance, the new synthetic method research of such compound always by
To the concern of chemists.Currently, such compound is mainly obtained by following approach: 1) benzindole -5- methoxyl group is de-
Methyl reaction；2) condensation-demethylating reaction of 1- (2- oxo -2- phenylethyl) pyridiniujm and 1- amino-4-methoxyl naphthalene；3)
The condensation reaction etc. containing active methylene compound such as 1,4- naphthoquinones and ethyl acetoacetate.Although these methods can be effective
Synthesis benzindole -5- alcohol compound, but there are still some urgent problems, such as: the Atom economy of reaction
Low, severe reaction conditions and complex for operation step etc., these shortcomings but also the practicability of the above method by very big
Limitation.In view of this, further studying and developing the letter for synthesizing benzindole -5- alcohol compound under mild reaction conditions
Prompt, efficient new method has important theory significance and application value.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of synthetic methods of aromatic ring diindyl -5- alcohol compound, should
Synthetic method passes through zinc powder using 5- oxo-benzindole -1- oxide or 5- Oxo-thiophen diindyl -1- oxide as raw material
The one pot of tandem reaction promoted directly obtains aromatic ring diindyl -5- alcohol compound, has easy to operate, mild condition, substrate
The advantages that applied widely, is suitable for industrialized production.
The present invention adopts the following technical scheme that solve above-mentioned technical problem, a kind of aromatic ring diindyl -5- alcohol compound
Synthetic method, it is characterised in that specific synthesis process are as follows: 5- oxo-benzindole -1- oxide 1 is dissolved in solvent, so
After zinc powder is added, in air atmosphere in -70 DEG C of room temperature react be made target product benzindole -5- alcohol compound 2, the conjunction
At the reaction equation in method are as follows:
Wherein R1For hydrogen, fluorine, chlorine, bromine, C1-4Alkyl or alkoxy, R2For phenyl, substituted-phenyl or thienyl, the substituted benzene
Substituent group on base phenyl ring is fluorine, chlorine, bromine, C1-4Alkyl or alkoxy, R3For hydrogen or C1-4Alkyl, R4For hydrogen or C1-4Alkyl, R are
C1-4Alkyl, the solvent are acetic acid, formic acid or propionic acid.
Further preferably, 5- oxo-benzindole -1- oxide 1 and the ratio between the amount of the substance that feeds intake of zinc powder are
1:3-10。
A kind of synthetic method of aromatic ring diindyl -5- alcohol compound, it is characterised in that specific synthesis process are as follows: by 5- oxygen
Generation-thiophene diindyl -1- oxide 3 is dissolved in solvent, and zinc powder is then added, in air atmosphere in -70 DEG C of reaction systems of room temperature
Obtain target product thiophene diindyl -5- alcohol compound 4, the reaction equation in the synthetic method are as follows:
Wherein R2For phenyl, substituted-phenyl or thienyl, the substituent group on substituted-phenyl phenyl ring is fluorine, chlorine, bromine, C1-4Alkane
Base or alkoxy, R3For hydrogen or C1-4Alkyl, R4For hydrogen or C1-4Alkyl, R C1-4Alkyl, the solvent are acetic acid, formic acid or third
Acid.
Further preferably, the ratio between the amount of the substance that feeds intake of the 5- Oxo-thiophen diindyl -1- oxide 3 and zinc powder
For 1:3-10.
Compared with the prior art, the present invention has the following advantages: (1) present invention by zinc powder promote 5- oxo-benzo Yin
The tandem reaction of diindyl -1- oxide or 5- Oxo-thiophen diindyl -1- oxide directly synthesizes aromatic ring diindyl -5- alcohols
Object is closed, whole process is easy to operate, high-efficient；(2) synthesis process has economical, green, right without using noble metal catalyst
Environmental-friendly feature；(3) Atom economy reacted is high, meets the requirement of Green Chemistry；(4) substrate is applied widely.
Therefore, the present invention provides a kind of economical and practical and environmentally protective new side for the synthesis of aromatic ring diindyl -5- alcohol compound
Method.
Specific embodiment
Above content of the invention is described in further details by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on above content of the present invention belong to this hair
Bright range.
Embodiment 1
Sequentially added in reaction tube 1a (0.5mmol, 160mg), solvent acetic acid (500 μ L) and zinc powder (2.5mmol,
163mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2a (116mg, 90%).It should
The characterize data of compound is as follows: mp:63-64 DEG C of1H NMR(400MHz,DMSO-d6) δ: 6.88 (d, J=2.0Hz, 1H),
6.99 (s, 1H), 7.28 (t, J=7.6Hz, 1H), 7.36-7.40 (m, 1H), 7.46 (t, J=7.6Hz, 2H), 7.52-7.56
(m, 1H), 7.92-7.94 (m, 2H), 8.16 (d, J=8.0Hz, 1H), 8.52 (d, J=8.4Hz, 1H), 9.42 (s, 1H),
11.73(s,1H).13C NMR(100MHz,DMSO-d6)δ:100.6,101.2,121.5,123.0,123.2,123.3,
123.6,125.0,125.3,126.0,127.0,127.2,129.3,133.1,136.4,147.4.HRMS calcd for
C18H14NO:260.1070[M+H]+,found:260.1051。
Embodiment 2
Sequentially added in reaction tube 1a (0.5mmol, 160mg), solvent acetic acid (500 μ L) and zinc powder (1.5mmol,
98mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2a (93mg, 72%).
Embodiment 3
Sequentially added in reaction tube 1a (0.5mmol, 160mg), solvent acetic acid (500 μ L) and zinc powder (5mmol,
327mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2a (106mg, 82%).
Embodiment 4
Sequentially added in reaction tube 1a (0.5mmol, 160mg), solvent acetic acid (500 μ L) and zinc powder (2.5mmol,
163mg), 4h is stirred to react in 50 DEG C in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2a (104mg, 80%).
Embodiment 5
Sequentially added in reaction tube 1a (0.5mmol, 160mg), solvent acetic acid (500 μ L) and zinc powder (2.5mmol,
163mg), 4h is stirred to react in 70 DEG C in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2a (82mg, 63%).
Embodiment 6
Sequentially added in reaction tube 1a (0.5mmol, 160mg), solvent formic acid (500 μ L) and zinc powder (2.5mmol,
163mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2a (79mg, 61%).
Embodiment 7
Sequentially added in reaction tube 1a (0.5mmol, 160mg), solvent propionic acid (500 μ L) and zinc powder (2.5mmol,
163mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2a (105mg, 81%).
Embodiment 8
Sequentially added in reaction tube 1b (0.5mmol, 175mg), solvent acetic acid (500 μ L) and zinc powder (2.5mmol,
163mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 2b (133mg, 92%).It should
The characterize data of compound is as follows: mp:70-71 DEG C of1H NMR(400MHz,DMSO-d6) δ: 3.88 (s, 3H), 6.84 (d, J=
2.0Hz, 1H), 6.98 (s, 1H), 7.20-7.28 (m, 2H), 7.45 (t, J=8.0Hz, 2H), 7.54 (d, J=2.4Hz, 1H),
7.88-7.91 (m, 2H), 8.46 (d, J=8.8Hz, 1H), 9.38 (s, 1H), 11.61 (s, 1H)13C NMR(150MHz,
DMSO-d6)δ:55.5,100.5,101.8,103.4,117.1,118.0,123.3,123.4,124.4,125.1,127.0,
127.4,129.2,133.3,135.6,146.7,155.9.HRMS calcd for C19H16NO2:290.1176[M+H]+,
found:290.1192。
Embodiment 9
Sequentially added in reaction tube 1c (0.5mmol, 177mg), solvent acetic acid (500 μ L) and zinc powder (2.5mmol,
163mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains white solid product 2c (124mg, 85%).It should
The characterize data of compound is as follows: mp:82-83 DEG C of1H NMR(400MHz,DMSO-d6) δ: 6.92 (d, J=2.4Hz, 1H),
6.99 (s, 1H), 7.38-7.42 (m, 1H), 7.51-7.58 (m, 3H), 7.93-7.97 (m, 2H), 8.17 (d, J=8.0Hz,
1H), 8.51 (d, J=8.0Hz, 1H), 9.49 (s, 1H), 11.80 (s, 1H)13C NMR(150MHz,DMSO-d6)δ:101.1,
101.2,121.5,123.0,123.4,123.5,123.6,125.0,126.1,126.8,127.2,129.3,131.5,
132.0,135.1,147.5.HRMS calcd for C18H13ClNO:294.0680[M+H]+,found:294.0692。
Embodiment 10
Sequentially added in reaction tube 3a (0.5mmol, 166mg), solvent acetic acid (500 μ L) and zinc powder (2.5mmol,
163mg), reaction 4h is stirred at room temperature in air atmosphere.Then 10mL ethyl acetate is added into reaction system and filters.Filter
Liquid ethyl acetate (15mL × 3) and saturated sodium carbonate solution (20mL) extraction, merge organic phase, dry with anhydrous magnesium sulfate.
Filtering, is spin-dried for, and crosses silica gel post separation (petrol ether/ethyl acetate=10:1) and obtains brown solid 4a (108mg, 80%).It should
The characterize data of compound is as follows: mp:82-83 DEG C of1H NMR(400MHz,DMSO-d6) δ: 6.65 (d, J=2.4Hz, 1H),
6.86 (s, 1H), 7.13-7.15 (m, 1H), 7.47-7.48 (m, 2H), 7.69 (d, J=5.2Hz, 1H), 7.81 (d, J=
5.6Hz,1H),9.65(s,1H),11.70(s,1H).13C NMR(150MHz,DMSO-d6)δ:99.9,100.0,121.5,
123.1,124.7,125.3,126.27,126.31,126.4,126.5,128.5,130.7,136.6,146.5.HRMS
calcd for C14H10NOS2:272.0198[M+H]+,found:272.0204。
Embodiment above describes basic principles and main features of the invention and advantages.The technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe originals of the invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (4)
1. a kind of synthetic method of aromatic ring diindyl -5- alcohol compound, it is characterised in that specific synthesis process are as follows: by 5- oxygen
Generation-benzindole -1- oxide 1 is dissolved in solvent, and zinc powder is then added, and is made in air atmosphere in -70 DEG C of room temperature reactions
Target product benzindole -5- alcohol compound 2, the reaction equation in the synthetic method are as follows:
Wherein R1For hydrogen, fluorine, chlorine, bromine, C1-4Alkyl or alkoxy, R2For phenyl, substituted-phenyl or thienyl, substituted-phenyl phenyl ring
On substituent group be fluorine, chlorine, bromine, C1-4Alkyl or alkoxy, R3For hydrogen or C1-4Alkyl, R4For hydrogen or C1-4Alkyl, R C1-4Alkane
Base, the solvent are acetic acid, formic acid or propionic acid.
2. the synthetic method of aromatic ring diindyl -5- alcohol compound according to claim 1, it is characterised in that: described
The ratio between amount for the substance that feeds intake of 5- oxo-benzindole -1- oxide 1 and zinc powder is 1:3-10.
3. a kind of synthetic method of aromatic ring diindyl -5- alcohol compound, it is characterised in that specific synthesis process are as follows: by 5- oxygen
Generation-thiophene diindyl -1- oxide 3 is dissolved in solvent, and zinc powder is then added, in air atmosphere in -70 DEG C of reaction systems of room temperature
Obtain target product thiophene diindyl -5- alcohol compound 4, the reaction equation in the synthetic method are as follows:
Wherein R2For phenyl, substituted-phenyl or thienyl, the substituent group on substituted-phenyl phenyl ring is fluorine, chlorine, bromine, C1-4Alkyl or alkane
Oxygroup, R3For hydrogen or C1-4Alkyl, R4For hydrogen or C1-4Alkyl, R C1-4Alkyl, the solvent are acetic acid, formic acid or propionic acid.
4. the synthetic method of aromatic ring diindyl -5- alcohol compound according to claim 3, it is characterised in that: described
The ratio between amount for the substance that feeds intake of 5- Oxo-thiophen diindyl -1- oxide 3 and zinc powder is 1:3-10.
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| CN106278989A (en) * | 2016-08-08 | 2017-01-04 | 河南师范大学 | The synthetic method of 3 cyanogen radical indole compounds |
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| ZH. V. CHIRKOVA ET AL.: "Chlorination of 2-substituted 1-hydroxyindoles", 《RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION》 * |
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